Ammonium Chloride → HCID 20148937, compound

HRID 569308Notes

Reaction equation

HRID 569308 reaction equation
[Na].[Cl:2][C:3]1[C:15]([Cl:16])=[C:14]([O:17][CH2:18][C:19]#[N:20])[CH:13]=[C:12]2[C:4]=1[C:5]1[C:10]([CH2:21][CH2:22][O:23]C(=O)C(F)(F)F)([CH2:11]2)[CH2:9][CH2:8][C:7](=[O:30])[CH:6]=1.[Cl-].[NH4+:32]>CO>[ClH:2].[Cl:2][C:3]1[C:15]([Cl:16])=[C:14]([O:17][CH2:18][C:19](=[NH:32])[NH2:20])[CH:13]=[C:12]2[C:4]=1[C:5]1[C:10]([CH2:21][CH2:22][OH:23])([CH2:11]2)[CH2:9][CH2:8][C:7](=[O:30])[CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 57042600HCID 57042600, compound

Product 1

HCID 20148937HCID 20148937, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of sodium metal (0.116 gm, 0.005 mole) in methanol (180 ml) was added {[5,6-dichloro-3-oxo-2,3,9,9a-tetrahydro-9a-(2-trifluoroacetoxyethyl)-1H-fluoren-7-yl)oxy}acetonitrile (8.20 g, 0.0183 mole). The reaction mixture was stirred for 11/4 hours in a nitrogen atmosphere then treated with ammonium chloride (2.0 g, 37 mMole) and stirring was continued for 21/2 hours. The methanol was evaporated in vacuo, the residue dissolved in water, allowed to stand for one hour, treated with 10N NaOH (10 ml), extracted with diethyl ether (100 ml) and then CH2Cl2 (3×50 ml), washed with water, dried over potassium carbonate and evaporated in vacuo. The residue was dissolved in diethyl ether, treated with a slight excess of ethanolic HCl, filtered under nitrogen, and washed with diethyl ether to give the {[5,6-dichloro-9a-(2-hydroxyethyl)-3-oxo-2,3,9,9a-tetrahydro-1H-fluoren-7-yl]oxy}ethanimidamide hydrochloride.

Workup

  1. stirringstirring
  2. custom2 hours
  3. customThe methanol was evaporated in vacuo
  4. dissolutionthe residue dissolved in water
  5. waitto stand for one hour
  6. additiontreated with 10N NaOH (10 ml)
  7. extractionextracted with diethyl ether (100 ml)
  8. washCH2Cl2 (3×50 ml), washed with water
  9. dry with materialdried over potassium carbonate
  10. customevaporated in vacuo
  11. dissolutionThe residue was dissolved in diethyl ether
  12. additiontreated with a slight excess of ethanolic HCl
  13. filtrationfiltered under nitrogen
  14. washwashed with diethyl ether

Sources & evidence

ORD record
ord-c338466543cb4741999e258e92a81fcb
Source dataset
uspto-grants-1988_03
Patent number
US04731471

Reaction notes

Loading…